Brett lost dozens of friends in base jumping — all sudden, unexpected deaths with no chance for goodbye. “They went around the corner and never came back.” This trained him into the practice of always saying goodbye as if it might be the last time, because it might be.

When his brother was diagnosed with terminal brain cancer, this created a paradoxical gift: for the first time, Brett had the opportunity to say the things that sudden death never allowed. His brother held Brett and his sister close and said, “It’s been an honor to grow up with both of you” — a moment that could only happen because they were acknowledging the reality of death rather than pretending it away.

Brett called his brother after the diagnosis and made an explicit choice: “There’s a reality where we could have spent the rest of our lives seeing each other every couple of years making small talk. And there’s a world where we can have a deeper relationship in one year than we ever would have had otherwise. Let’s lean into that.”

“If we were not acknowledging the possibility that anytime I see him could be the last, we wouldn’t be having the kinds of conversations that we’ve had.”

The practice applies to every relationship, not just those facing visible death — because all relationships are impermanent, and all goodbyes might be the last.

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